


The Trickster is Back In Town, Playing Matchmaker.

by Castiel_savvy18



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Boners, Confusion, Embarrassed Castiel, Embarrassed Dean, First Kiss, First Time Blow Jobs, Fluff, Fluff and Smut, Gender Confusion, M/M, My First Fanfic, Porn, Sam Winchester Ships Castiel/Dean Winchester, Sexual Confusion, Smut, Tied-Up Castiel, Trickster Gabriel
Language: English
Status: In-Progress
Published: 2016-09-04
Updated: 2016-09-10
Packaged: 2018-08-13 01:38:02
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 4
Words: 2,436
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7957141
Author URL: https://archiveofourown.org/users/Castiel_savvy18/pseuds/Castiel_savvy18
Summary: <blockquote class="userstuff">
              <p>The Trickster is back in town. He was bored, and he wanted to mess with his brother, he planned everything out, and was hoping it will end with him being satisfied.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Bear with me, this is my very very first time making a Fanfiction. Ever. So I would appreciate feedback, negative and positive.

Dean was talking to Sam and Bobby,  
"So how can we kill it?" Dean asked  
"Well, that I'm not sure of. Do you think I know everything idjit." Bobby replied.

"I just figured you would know because all you do is sit at home and drink."

"That escalated quickly.." Sam said, trying to get them to stop.

"To kill a Trickster one must obtain a stake dipped in the blood of its victim and stab it into the Trickster's heart..." Castiel said suddenly appeared, making Dean jump.

"Um... Thanks Cas." Dean said.

Suddenly Dean felt a heavy weight in his back and his face falling first to the floor.

"W-what the hell!?" Dean yelled.  
Dean looked over his shoulder only to find Cas laying on top of him.

"C-Cas, can you get off- ugh- of me?" Feeling his ribs pressing against the wooden floors, struggling to breath, do to the heavy weight on his back.

"My apologies." Cas said getting onto his feet.

Dean looked at Bobby and Sam, only to see them smirking. 

"What!?" Dean said angrily

"Nothing," Sam said looking at Cas then Dean, chuckling under his breath.  
"I'm curious. Cas, why did you fall on top of him?" Sam said, still smirking.

"I-I'm not sure..." Castiel replied worried, tilting his head to one side.  
"It-it felt like I was pushed.."

"Well, no one was there. Who the hell would do this!?" Dean yelled.

"I-I'll, uh, go figure that out.." Cas said, then shortly disappearing.


	2. Hiding Feelings

**Summary for the Chapter:**

> They have come to conclusion it was indeed the one and only, The Trickster, Gabriel. Dean attempts to hide the truth, but the trickster has plans to spill it.

**Notes for the Chapter:**

> I'm trying my best. First time. Please give feedback. Thank you.

"It is the Trickster." Castiel said staring at Bobby trying to avoid contact with Dean.  
"Great. So... What now?" Sam asked.  
Before castiel could answer, he felt a hand crawl up his back and back down to his ass grabbing it.  
Sam watched with a weird look, not knowing what was happening.  
Castiel is squirming uncomfortably as the hand made its way to his cock. Causing Cas to slightly moan.  
The invisible hand stopped suddenly, and Cas turned to Sam, acting like nothing happened.

"I-I think.. Summon him?" Cas said asking it as a question.

Sam and Bobby grabbed all the materials they needed to summon Gabriel, chanting and waiting about a minute until he finally appeared.  
"STOP THIS GABRIEL!" Dean yelled loudly when he first saw the Trickster. 

Castiel instintly looked over at Dean with a look that says 'You just fucked up.'

"G. Hello to you too Dean." Gabriel said in a sarcastic voice.  
"So, Castiel..., did you enjoy the hand grabbing?" Gabriel asked with one brow raised, smirking.

"Why?" Cas asked.  
"Why what?" Gabe said with a smirk still on his face.  
"You know what!..." Cas said, starting to get angry.  
Dean jumped in,

"Stop this. Stop this RIGHT NOW!" Dean yelled viciously.

"Nope. And I still have more to come. This is only just the beginning." Gabriel said as he disappeared.  
"SON OF A BITCH!" Dean yelled.

_____________________________

That night, Dean began to have strange dreams. Very strange.  
Castiel was on top of him, kissing him from the neck leaving a mark, claiming him. He started kissing his chest to his belly button. Cas started to touch his bulge in Dean's jeans.  
Little did Dean know, he was making strange noises.  
"CAS!" Dean moaned very loudly.  
Sam wasn't in the motel room, but Cas was. He looked at Dean with a look of shock. He didn't know if he should wait it out or wake Dean up and see if he was okay.  
Dean's dream continued,  
Castiel started unbuckling Dean's pants, slowly pulling it down and left Dean in only his bokers. Cas grabbed Dean's very wet, hard bulge. Dean started to moan again in real life,  
"OH CAS!!! CAS! UGH! OH ANGEL!" Dean screamed and moaned.  
Castiel was very worried at this point and thought he should wake him, until he heard Dean panting and saw in the sheets something raised. Creating a little tent.  
He walked over slowly, and felt a feeling in his stomach when he heard Dean screaming his name once more and panting hard.  
He closed his eyes trying to wash away the feeling, still hearing Dean pant. He had to wake him up now. He couldn't listen any longer.  
"Dean.., Dean.." Cas said in Dean's ear while pushing on his shoulders.  
"Wha-what...?" Dean awoke and saw Cas looking at him with a embarrassed, mixed with curious look on his face.  
Castiel turned away, trying not to look down at Dean's 'tent'.  
Dean looked down and saw his boner, he instantly turned over trying to cover it up from Cas.  
"Cas... How- uh- how long have you been here?"  
"For awhile..." Cas said very quietly still facing his back to Dean.  
Cas quickly flapped his wings and he was gone. Leaving Dean alone, embarrassed.  
Dean sighed, and felt the wetness in his boxers.  
What was wrong with him? He was straight. Not bi or gay. Why did he dream about Cas and enjoying it?  
Dean thought back to the dream, images going through his mind of Castiel going down on him. He couldn't stop. But he knew it was just the trickster doing this to him.  
Or was it?


	3. Closet Time

**Summary for the Chapter:**

> The Trickster trapped Dean and Castiel in a Closet, making them get a little too close...

"Cas... Can you back up a bit?" Dean asked cautiously.

> "My apologies Dean. But... I can't. It's.. It's too small." Cas said.
> 
> "Well, can you try to?" Dean asked.

Cas attempted to back up a bit but it seemed the closet got even smaller, and Cas's body was pressed up against Dean's more.

> "Damn it Cas!" Dean yelled.
> 
> "Dean, I'm terribly sorry... The closet seemed to have gotten smaller." Cas replied softly.

Dean attempted to try and turn around to look at his surroundings, but he only made it more awkward. His ass kept rubbing up against Cas's growing hard bulge. Making Dean wince.

> "Uh... Sorry Cas." Dean said, cringing.
> 
> "I-it's okay..." Cas said with a very, very quiet moan trying to hold back his blush, but his face grew red.

Dean noticed him blush, causing Dean to blush back. Dean turned fully around touching Cas in wrong places by accident. They're faces were centimeters apart. Nose's almost brushing. 

Cas smiled awkwardly at Dean. And Dean smiled back, while blushing.

> "Dean?.... What do we do now?" Cas asked breaking the silence.
> 
> "wait it out?... I don't know." Dean replied.
> 
> "Dean, my brother wants to be pleased... We won't get out of this situation unless we please him. Dean, the closet is getting smaller as we speak." Cas said with a head tilt, looking into dean's green eyes.
> 
> "So, what do we do?" Dean said. But he knew what they had to do. They had to kiss.

Dean leaned forward without Castiel able to reply to his question. Dean grabbed Castiel's face, and leaned forward,

The door flew open suddenly, Sam standing there and set them free. Cas was actually giving Sam a glare. He wanted to kiss Dean. Badly.

But, his brother Gabr wasn't gonna stop there, so he smiled at the thought that they will eventually kiss.

> "Thanks Sammy. You always got my back." Dean said to Sam with a pat on the shoulder, faking a smile.

He wanted to kiss Cas too...

 

**Notes for the Chapter:**

> Please leave feedback. :) thank you.


	4. Reveled

**Summary for the Chapter:**

> Dean get's what he wants from Cas, and Cas gets what he wants. They both reveal there secrets to each other.

**Notes for the Chapter:**

> Hope you like!

Dean couldn't help but think about the closet. Feeling Cas' body up against him. He wished Sam never came. He was about to kiss Cas, but was interrupted.

He thought about everything and started to get hard. Then he heard a flap of wings and a cool breeze wash over him.

> "Hello Dean." Cas said in his dark gravely voice.

Dean quickly covered his waist with the blankets, trying to hide his hard on in his sweatpants. But Cas already noticed.

> "Oh, hey Cas..." Dean said with a nervous tone.
> 
> "Dean. We need to talk."
> 
> "Yeah. What is it?" Dean said still with a nervous tone. 

_Oh god... Was he going to talk about the closet.. Dean thought to himself._

> "Yes Dean I am." Cas said replying to Dean's thought.
> 
> "You heard me...?" Dean said with his eyebrows raised
> 
> "Yes. I always was able to." Cas said seriously.
> 
> "Y-You hear everything..." Dean said.
> 
> "Yes."
> 
> "Fuck..." Dean mumbled under his breath. He would've said it in his head, but either way Cas would still hear him.
> 
> "Dean, it's not your fault. Human's need pleasure. It's nothing to be ashamed of... Thinking about me... That way.." Cas said having a hard time saying it.
> 
> "I have thoughts too Dean..." Cas added.

Dean sat there with his eyebrows raised. It made him get even more hard knowing Cas thinks like that...

 _Does he think about me?..._ Dean thought. But he knew Cas heard that. He hoped he did actually. He wanted to know.

> "Dean... When we were in the closet..." Cas paused getting prepared for what he was going to say. "I thought very dirty things, Dean. Dirty things about you..."

Dean's Cock was aching now. Hearing that from Cas. That really turned him on.

Dean pulled the blankets off of him, not caring if Cas see's his boner. He got up off the bed, and slowly walked towards Cas.

Cas couldn't help but stare at Dean's hard on with wide eyes. He lightly moaned under his breath hoping Dean didn't hear. But he did.

> "You like?" Dean said with a sexy tone. Making Cas ache in his pants, his Cock begging to be touched.
> 
> "D-Dean...I should go..." Cas said nervously.
> 
> "NO!" Dean yelled.
> 
> "Cas, stay. Stay with me." Dean said.

Cas backed up a bit, and nervously looked around the room. Hoping to find dorm thing to distract himself from looking at Dean's lower body. But Dean walked towards him. 

This time, Dean got in Cas' personal space. It's usually the other way around.

> "I think it's time to kiss. We never got to since Sam interrupted." Dean said winking at Cas.

"Uh.." Cas didn't know what to say. 

Dean walked closer to Cas, and grabbed his waist. He licked his lips, making Cas get even more turned on. Oh he wanted Dean so badly. But his father would not approve. Ugh. Fuck his father.

Cas grabbed Dean's face and pulled it forward kissing him aggressively. He could feel Dean smirking. Dean wrapped one hand around Cas' waist and the other on his cheek. He licked Cas' lips asking to enter. Cas parted his lips allowing Dean to put his tongue in Cas' mouth. They fought for dominance. Dean backed away from the kiss panting for oxygen. He now wrapped both hands around Cas' waist. Slowly moving his hand down, grubbing Cas' ass.

> "So firm." Dean whispered into Cas' ear.

Dean backed up and started taking his grey v-neck shirt off. Cas gasped at how muscular Dean was. He wanted to see more. But he didn't want to make the move.

 

> "Dean..." Cas moaned quietly.

Dean put his hands under Cas' shirt and wanted to see more. Cas giggled at how ticklish he was when Dean touched him. Dean threw Cas' shirt off and throwing it to where his shirt laid.

Dean slowing rubbed his hands up and down Cas' chest, admiring how muscular he was. He was shocked. His hands slowly made it down to his waistline. He grabbed Cas' belt loop and pulled him closer. He stared into the Angel's beautiful blue eyes, as he started unbuckling Cas' belt. Dean pulled Cas' pants down and Cas stepped out of them.

Cas did the same thing to Dean. They were now standing there only in their boxers.

Dean's hands found there way to Cas' boner. He cupped it, and rubbed slowly.

> "More D-D-Dean!" Cas begged.
> 
> "Patience Love." Dean said with a husky voice.

Cas couldn't take it anymore and he ripped Dean's boxers off. Stepping back to admire how big it was. He gasped at the size, and moaned very loudly. 

Dean ripped Cas' boxers off, and saw that his size was big too. It turned him on so much, Dean started dripping pre-cum.

Cas grabbed Dean's dick and starting rubbing it making Dean moan his name.

He moved his free hand towards Dean's entrance, and slowly putting one finger in. Causing Dean to slightly wince in pleasurable pain.  
Cas fingered him in and out and repeated it with two fingers, then three. He curved his fingers in, accident hitting Dean's prostate. Making Dean moan loudly. Cas grinned that he found his sweet spot.  
"M-more..." Dean begged.  
Cas slowly eased out his fingers and Dean wimpered from the loss. Cas proceeded to slowly slip his way into Dean's entrance. Taking a pause to get himself comfortable and Dean to be comfortable.  
"Dean." Cas said, with questionable blue eyes.  
Dean nodded at Cas to proceed, telling him he was ready to go.  
Cas almost fully pulled out, but then thrust led into Dean hard making the bed shake and Dean moan.  
"Ugh! Cas! More! Faster!" Dean begged in a demanding gravely voice.   
Cas pleased Dean for what he wanted, and thrusted into Dean over and over again fast, and hard. The bed was screeching and moving, Dean's head slightly almost hitting the headboard.  
Cas felt slight butterflies in his stomach, and moaned quietly.  
"Ohhh Dean..."  
Cas felt like he was going to climax soon.  
Cas gripped onto Dean's dick and began slowly stroking it. He increased the speed to sync with his thrusts. Dean felt like Cas had taken control over his entire body.  
"Oh! CASTIEL!" Dean screamed with a loud moa . Reaching his climax, and spilling sticky white substance over both of their stomachs.  
Cas then orgasmed and released himself filling Dean up.  
"OHHHH! DEAN!!!" Cas screamed loudly.   
Cas swung back his head and panted loudly. He then collapsed onto Dean and slowly pulled himself out of Dean.  
"C-Cas...," Dean started then paused trying to catch his breath. "That. Was. Amazing..." Dean finished with a smile across his face.  
"I know." Cas said with a smirk, seeming to be bragging about his talents.  
"Cas?" Dean asked.  
"Hmm." Cas said into Dean's chest.  
"I-I think I l-l-love you..." Dean said struggling to make out the words. He never thought he would EVER say that to a MAN. An angel. Castiel. But he knew those words were true.   
"Dean..." Cas sighed. Relieved. "I love you too. In fact, for a very long time. I never admitted it, but I have always secretly loved you." Cas said with caution. Dean smirked and pulled Cas' face up towards him, kissing him softly.  
"Me too." Dean said into Cas' mouth.  
"Always" Dean said after releasing from the romantic kiss.   
He never thought he would kiss a man. He never thought he would kiss Castiel.... But he did. And he loved every second.

**Author's Note:**

> I hope you enjoyed... please give me ideas, and how to do better with my story. Please and thank you.


End file.
